Where you've seen him: NBC's Parks and Recreation

Aziz told us in 2011 that Kanye West usually makes fun of what he wears. "One time I saw him and I had on a brown leather jacket. He was like, 'Ha-ha—you look like a regular dude!'" And it's true—in a good way. There isn't anything particularly flashy about his style but that's what we like about it. His look isn't completely out of reach for other regular dudes. The stand-up comedian, Twitter loudmouth, and Parks and Recreation actor frequents in leather jackets, crisp button ups, sharp Band of Outsiders suits, Moscot glasses, and Comme des Garçons Play Jack Purcell sneakers.